85520-67-8Relevant academic research and scientific papers
Pd(II)-Catalyzed CC Bond Cleavage by a Formal Group-Exchange Reaction
Ye, Runyou,Zhu, Maoshuai,Yan, Xufei,Long, Yang,Xia, Ying,Zhou, Xiangge
, p. 8678 - 8683 (2021/07/26)
A chelation-assisted palladium-catalyzed CC bond cleavage of α, β-unsaturated ketone to form alkenyl nitrile in the presence of nitrile is disclosed on the basis of a formal group-exchange reaction formulated as C1C2 + C3 → C1C3 + C2, differing from normal alkene oxidative cleavage and metathesis type. The isolated key active Pd(II) complex as well as deuterium-labeled experiment revealed the necessity of the chelation group, and a plausible catalytic pathway was proposed.
Alkenenitrile transmissive olefination: Synthesis of the putative lignan "morinol I"
Fleming, Fraser F.,Liu, Wang,Yao, Lihua,Pitta, Bhaskar,Purzycki, Matthew,Ravikumar
, p. 6843 - 6846 (2012/01/06)
Grignard reagents trigger an addition-elimination with α′- hydroxy acrylonitriles to selectively generate Z-alkenenitriles. The modular assembly of Z-alkenenitriles from a Grignard reagent, acrylonitrile, and an aldehyde is ideal forstereoselectively synthesizing alkenes, as illustrated in the synthesis of the putative lignan morinol I.
An α-Diaminoboryl carbanion assisted stereoselective single-pot preparation of α,β-disubstituted Acrylonitriles
Tomioka, Takashi,Sankranti, Rambabu,Vaughan, Trey G.,Maejima, Toshihide,Yanase, Takayoshi
experimental part, p. 8053 - 8058 (2011/11/28)
An α-diaminoboryl carbanion-mediated one-pot olefination directly converts an acetonitrile or the homologous nitrile into a series of α,β-disubstituted acrylonitriles in a stereo-selective manner. The protocol involves the formation of an α-substituted α-diaminoboryl acetonitrile and subsequent olefination with an aldehyde. The use of an aryl or conjugated aldehyde preferentially leads to a (Z)-acrylonitrile, while an aliphatic aldehyde gave an (E)-isomer as a major product. Two complementary approaches, a linear method and a divergent method, are developed.
Applications of the Baylis-Hillman Reaction 2: a Simple Stereoselective Synthesis of (E)- and (Z)-Trisubstituted Alkenes
Basavaiah, Deevi,Sarma, Pakala K. S.,Bhavani, Anagani K. D.
, p. 1091 - 1092 (2007/10/02)
Reaction of Grignard reagents with methyl 3-acetoxy-2-methylenealkanoates produces (2E)-2-substituted alk-2-enoates, whereas a similar reaction with 3-acetoxy-2-methylenealkanenitriles provides (2Z)-2-substituted alk-2-enenitriles in high (Z)-stereoselectivity.
Lewis Acid Mediated Synthesis of 2-Alkenenitriles Using C,N-Bis(trimethylsilyl)ketenimine and Carbonyl Compounds
Matsuda, Isamu,Okada, Hisashi,Izumi, Yusuke
, p. 528 - 532 (2007/10/02)
2-Substituted 2-alkenenitriles are obtained in the condensation reaction of carbonyl compounds with C,N-bis(trimethylsilyl)ketenimine in the presence of Lewis acid.The combination of tris(trimethylsilyl)ketenimine and aldehydes results in the high E-selective formation of 2-trimethylsilyl-2-alkenenitriles.Among some Lewis acids, magnesium bromid gives the best E-selectivity in the formation of 2-trimethylsilyl-2-undecenenitrile.Stereospecific protodesilylation of 2-trimethylsilyl-2-alkenenitriles in an aqueous methanol solution of potassium fluoride accomplishes a new route to (Z)-2-alkenenitriles from aldehydes.
